Caldwells Add Homes for Sale

Caldwells Add Homes for Sale

Welcome to Caldwell's Addition, a charming subdivision nestled in the heart of Ocala, Florida, in Marion County. This delightful community offers a perfect blend of suburban tranquility and urban convenience, making it an ideal choice for families, retirees, and everyone in between.

Caldwell's Addition is characterized by its tree-lined streets, friendly neighbors, and a warm sense of community. Residents enjoy the benefits of living in a peaceful environment while being just a stone's throw away from Ocala's vibrant downtown area, where shopping, dining, and entertainment options abound. The area is also known for its proximity to beautiful parks and recreational facilities, perfect for outdoor enthusiasts and families looking to enjoy sunny Florida days.

Currently, there are a variety of homes for sale in Caldwell's Addition, catering to diverse tastes and budgets. Whether you’re in the market for a cozy starter home or a spacious family residence, you’ll find options that suit your needs. Many properties feature modern amenities, inviting layouts, and beautifully landscaped yards, ensuring that you can find the perfect space to call home.

The community’s appeal is further enhanced by its excellent schools, healthcare facilities, and easy access to major highways, making commuting a breeze. With its welcoming atmosphere and prime location, Caldwell's Addition presents an exceptional opportunity for homebuyers seeking a slice of Florida paradise. Explore the homes for sale today and discover the charm and convenience that this delightful subdivision has to offer!

Newest Caldwells Add Homes for Sale

2 Beds ⋅ 1 Baths ⋅ Caldwells Add SubDv. ⋅ 34471 Zip Code

Full-sized, genuine historic grandeur set in a minimized abode. Truly lavish for a home with small stats, this 2 bedroom 1 bath with a hard-to-beat downtown location is a perfect starter, an estate down-size, or a central Florida vacation nook with tons of possibilities. With modern amenities, enhanced bungalow charm and just a three block proximity to the Ocala market, you won’t find anything in this prized Historic District with a more attainable price point and a more welcoming, single-story oasis to steal away to at the end of the day. Private and exploding with oversized exterior living space, this one is a day napping in a garden hammock or your evening bistro decked out for social gatherings. Large rooms, stunning heart pine wood, high-ceilings with picture rail and over 2100sf under roof gives this wee historic home a buff profile. Favorite modern twists include a triple-headed marble shower room with built in bench seating, tankless gas hot water heater, nearly 500sf of rear multi-level decking off the new kitchen, and stainless steel appliances. An indoor laundry with its own sink, two fireplaces, mature landscaping, a grand front porch with attached porte-cochere, and a detached garage/workshop with electric, round out your new home. You’re just in time for the holiday golf cart parades! Established, bonded 'community feels' in the heart of Ocala. Zoned R3, this property also offers multi-family flexibility and investment potential beyond the genuine impact of residing in one of Ocala’s earliest memories.

818 Se 3rd Street, Ocala

3 Beds ⋅ 2 Baths ⋅ Caldwells Add SubDv. ⋅ 34471 Zip Code

Nestled in the walkable, golf cart–friendly Historic District of downtown Ocala, this beautifully renovated home blends timeless character with modern conveniences. Boasting three bedrooms, one full bath and one half bath, it’s the perfect balance of era-appropriate detailing and contemporary upgrades. The interior is completely renovated with new wiring and plumbing, a stylish new kitchen with modern appliances, and updated fixtures and finishes throughout, while preserving charming historic accents. Located in a golf cart and walking-friendly neighborhood, the home is just a short stroll or ride to shops, dining, and major medical facilities, with central access to Ocala’s vibrant downtown scene and parks. The exterior and interior balance preserved architectural details—moldings, trim, and vintage touches. The outdoor spaces are low-maintenance, with parking options available in a neighborhood known for its downtown charm. This property presents a strong move-in-ready option with turnkey updates and modern conveniences, plus solid investment potential for buyers seeking a historic, character-filled home in a coveted area. If you’re looking for a downtown Ocala residence that honors its history while delivering contemporary practicality, this renovated 3BR/1.5BA charmer in the Historic District is worth a look.

819 Se 2nd Street, Ocala

3 Beds ⋅ 2 Baths ⋅ Caldwells Add SubDv. ⋅ 34471 Zip Code

Historic charm, an unbeatable location, and a front porch worth slowing down for! Located just a few short blocks from the Downtown Market, Ocala’s Historic Downtown Square, splash pad, award-winning restaurants, boutiques, special events, and so much more, this bungalow offers the best of downtown living. Pride of ownership is evident throughout this 3 bedroom, 1 1/2 bath home, where original wood trim, moldings, built-in shelving, and wood floors preserve the warmth and character of its historic roots. A light-filled bonus room adds flexible living space and is framed by oversized double-paned wood windows, creating the perfect spot for a reading nook, home office, art studio, or exercise space. Out back, the large deck provides ample room to relax, entertain, and soak up the Florida sunshine. Additional features include a carport with room for your golf cart — fitting for this golf cart-friendly neighborhood — plus storage and workshop space for hobbies, tools, or weekend projects. Classic bungalow character, thoughtful updates, and a downtown lifestyle come together in one truly special Ocala Historic District home. Roof 2022. HVAC 2021.

505 Se Sanchez Avenue, Ocala

4 Beds ⋅ 4 Baths ⋅ Caldwells Add SubDv. ⋅ 34471 Zip Code

WELCOME TO THE HISTORIC OSBOURNE HOUSE RARE OPPORTUNITY TO OWN THIS ICONIC 1922 VICTORIAN TWO-STORY TREASURE IN ITS TRADEMARK PINK COLOR SCHEME. WHERE TIMELESS CHARM MEETS MODERN OPPORTUNITY. PERFECTLY POSITIONED AND RICH WITH CHARACTER, THIS STANDOUT PROPERTY IS CURRENTLY ZONED HISTORIC RESIDENTIAL COMMERCIAL (RBH-3) AND OFFERS INCREDIBLE FLEXIBILITY, WITH ELIGIBILITY TO REZONE TO RBH-1, 2, OR 3 TO SUIT YOUR VISION & PURPOSE. WHETHER YOU’RE DREAMING OF A DISTINCTIVE RESIDENTIAL HOME. A LIVE-WORK SPACE, BOUTIQUE PROFESSIONAL OFFICES, OR AN ENCHANTING BED & BREAKFAST, THE POSSIBILITIES HERE ARE AS EXPANSIVE AS THE HOME ITSELF. INSIDE, YOU’LL FIND A GENEROUS, ADAPTABLE FLOORPLAN READY TO BE TAILORED TO YOUR NEEDS—BLENDING VINTAGE ELEGANCE WITH MODERN FUNCTIONAL VERSATILITY. THIS IS MORE THAN A PROPERTY—IT’S AN EXPERIENCE. FROM ITS EYE-CATCHING EXTERIOR TO ITS INVITING INTERIOR SPACES, EVERY DETAIL INVITES YOU TO IMAGINE WHAT COULD BE. A TRUE MUST-SEE TO FULLY APPRECIATE. BE SURE TO EXPLORE THE IMMERSIVE 3D TOUR ATTACHED TO THE LISTING FOR A REAL-TO-LIFE PREVIEW. OPPORTUNITIES LIKE THIS ARE RARE—CALL TODAY TO SCHEDULE YOUR PRIVATE SHOWING AND BRING YOUR VISION TO LIFE.

805 E Fort King Street, Ocala

4 Beds ⋅ 2 Baths ⋅ Caldwells Add SubDv. ⋅ 34471 Zip Code

Located in Ocala’s Historic District and Golf Cart District, just 4 blocks from the Downtown Farm Market, this 2-story cottage is full of charm, character, and potential. The current floor plan configuration offers 3 bedrooms and 2 bathrooms, with the primary bedroom and both full baths on the first floor, plus 2 bedrooms and a bonus room upstairs. Original features include wood floors in many rooms, high ceilings, a fireplace in the formal living and dining area, and a double fireplace shared by the family room and primary bedroom. The cottage is positioned on the parcel with ample room for a future garage and/or pool. This home is ready for updates and restoration making it an exceptional opportunity for a buyer with vision to create a dream home in one of Ocala’s most sought-after historic neighborhoods.

721 Se 5th Street, Ocala

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Kenneth Weir

With over 20 years of experience in New York, Kenny brings deep market knowledge, sharp negotiation skills, and a client first approach to every transaction. In February 2025, I relocated to Ocala, Florida where I quickly earned my Florida Real Estate license in March 2025 and began helping buyers and sellers confidently navigate the market in the Horse Capital of the World. For several years while working with clients in the Real Estate market in NYC and Long Island I worked for a title company as a settlement closer.This background gave me a unique advantage. I understand contracts,title issues, and the closing process from the inside out. My clients will experience the benefit of smoother transactions, fewer surprises, and strong protection from start to finish.I'm known for my clear communication, honest guidance, and dependable service. I focus on making the buying or selling experience as stress-free as possible. Whether working with first-time buyers, relocating families, or seasoned investors I am committed to helping clients make smart real estate decisions and feel confident every step of the way.

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